I've had a few ideas that I keep in a text document, but I don't have the skills to make them anything more than ideas. Here are two that I'm pretty satisfied with. 1.) Somewhere along the roads, you're approached by a dirty, frazzled looking man. He asks for your help in finding a powerful sword that he'd purchased from a traveling merchant and buried long ago for safe-keeping. The problem is that he can't remember where he buried it! He promises to pay you a sum of gold in return for your assistance in the search. You follow him from location to location while he shares his knowledge of the great many conspiracies against him and the people of Skyrim. Each time you arrive at a new spot, he'll kneel down and search, only to find nothing and come up with a different idea of where to look next. Suddenly, he seems to finally remember exactly where he put it! He hurries off, and upon following him, you find yourself at the exact same spot he approached you for help. Eager to see the sword for yourself, you ask him to open the chest. The man becomes angry. He asks you if you've been following him this whole time, and why!? You must be trying to steal sword for yourself! He pulls the sword from the chest and attacks you. You raise your weapon to defend yourself, and as you strike him down, you realize that this supposedly powerful sword is nothing but a child's toy: a wooden sword. If you search his body, you'll find his notebook filled with ramblings and nonsense about those who conspire against him. If you search the chest, you'll find a paltry sum of gold, a fork and knife, and a sweetroll. 2.) Sitting next to one of the signposts around skyrim's roads, a man calls out to you and asks if you can spare a few coins. If you approach him, you'll ask him what he needs the money for. He nervously responds that he hasn't had a hot meal or soft bed in a few days, but he seems to be lying. If you pass a Persuasion or Intimidation check, he reveals that he intends to use the money to purchase skooma. He tells you how he first tried it on the night of his son's birth to celebrate, and goes on to tell you about his descent into addiction and how he abandoned his family. Too ashamed to return home, he wanders from town to town, spending most of what little money he gets on more skooma. He asks you again to spare him a few coins, saying he needs the skooma to survive. You're then presented with 5 choices: --persuade him to follow you to whiterun, where you will bring him to the temple of kynareth to seek treatment and guidance --intimidate him to go to whiterun himself --give him the money --simply tell him that you won't help him, after which you go on your way --insult him and attempt to leave, only to have him attack you --If you persuade him, he'll follow you to the temple and thank you for your help. After some time, you'll receive a letter from him thanking you again. He tells you that he hasn't had skooma since you last saw him and plans to return home soon --If you intimidate him, he'll run off and you'll simply never see/hear from him again. --If you give him the money, he'll thank you and you'll never see/hear from him again. --If you refuse to help, he'll plead with you one last time as you leave. Later, when you approach a city with a khajiit caravan, you'll see him attack the khajiit and be struck down. --If you insult him, he'll attack you and either kill you or be killed (much more likely) I'm not particularly sure about the logistics on these, but if you like them and they seem doable, I hope they can be useful. EDIT: Added the option to just give the beggar some money per Xander9009's suggestion.